On-site
Financial
jobscollider
About this role
About Gusto
At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.
All full-time employees receive competitive base pay,
benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.
AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience
requirements vary by role and will be assessed during the interview process.
About the Role:
We are seeking a highly motivated and licensed Property & Casualty (P&C) Insurance Broker to join our team as part of a critical pilot to launch a P&C broker model at Gusto. You will be essential in evolving Gusto’s business insurance channel by acting as a licensed agent to quote and issue business insurance policies with our NEXT Insurance carrier partner.
You will use your expertise to provide direct support and an improved experience for small business customers with complex insurance needs, helping to capture meaningfully higher revenue and accelerating the development of our AI Insurance Advisor.
About the Team:
This team is crucial to solving customer experience gaps and optimizing our offline insurance channels. You will be a SME who is part of the “human-in-the-loop” workflows required to train and optimize Gus as an AI insurance advisor. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot being key to establishing our digita
Commission Structure
Base Salary
$,k
Commission
Structure not specified
Ramp Period
Not mentioned — clarify timeline
Accelerators
Yes
Selling Motion
Prospecting
Channel / Partner
Sell through partners, resellers, or alliances
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Ownership stake offered
Financial Services — Interview Intel
Typical Sales Cycle
3–6 months (Retail) · 6–18 months (Institutional)
Common Buyer Objections
- "Regulatory concerns — need compliance approval"
- "We already have a vendor for this"
- "Need to see 3-year track record"
- "Committee-based decision — multiple approvers"
Key Industry Metrics
Hot Topics to Reference
- • AI in fraud detection and compliance
- • Open banking APIs
- • ESG investing mandate shifts
- • Embedded finance partnerships
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Gusto, you'll own the entire revenue pipeline and be measured on quota attainment.
Trust-building is paramount — prospects need confidence in your expertise.
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